Sodium borohydride → (S)-N-Benzyl-N-methyl-2-[N-(t-butoxycarbonyl)-2-hydroxy-ethylamino]-3-phenyl-propionamide

HRID 235543Notes

Reaction equation

HRID 235543 reaction equation
[CH2:1]([N:8]([CH3:30])[C:9](=[O:29])[C@@H:10]([N:18]([CH2:26][CH:27]=[O:28])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C.C(OCC)(=O)C>[CH2:1]([N:8]([CH3:30])[C:9](=[O:29])[C@@H:10]([N:18]([CH2:26][CH2:27][OH:28])[C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 53842533(S)-N-benzyl-N-methyl-2-[N-(t-butoxycarbonyl)-2-oxo-ethylamino]-3-phenyl-propionamide

Product 1

HCID 54174094(S)-N-Benzyl-N-methyl-2-[N-(t-butoxycarbonyl)-2-hydroxy-ethylamino]-3-phenyl-propionamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine (S)-N-benzyl-N-methyl-2-[N-(t-butoxycarbonyl)-2-oxo-ethylamino]-3-phenyl-propionamide (5.0 mmol) and sodium borohydride (5.0 mmol) in ethanol (20 mL). Stir for 16 hours. Concentrate in vacuo to obtain a residue. Dilute the residue with ethyl acetate and extract with 0.5M hydrochloric acid solution and water. Separate the layers, dry the organic layer over MgSO4, filter, and evaporate in vacuo to give the title compound.

Workup

  1. concentrationConcentrate in vacuo
  2. customto obtain a residue
  3. extractionextract with 0.5M hydrochloric acid solution and water
  4. customSeparate the layers
  5. dry with materialdry the organic layer over MgSO4
  6. filtrationfilter
  7. customevaporate in vacuo

Sources & evidence

ORD record
ord-60c3190e76c34543b4512c29e6c4bbc4
Source dataset
uspto-grants-1997_01
Patent number
US05597845

Reaction notes

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